3867-15-0Relevant articles and documents
Synthesis and antinociception properties of phencyclidine derivatives with modified aromatic or cycloalkyl rings and amino group
Ahmadi, Abbas,Khalili, Mohsen,Barzin, Mahnaz,Pooladi, Mohsen,Bakhtiari, Fatemeh,Barjeste, Maede,Nahri-Niknafs, Babak
, p. 457 - 464 (2016)
Phencyclidine is an arylcyclohexylamine compound which has received a lot of investigative attention due to the complex spectrum of behaviours and its complicated interactions with the central nervous system. Phencyclidine administration may act as stimulant, depressant, hallucinogen, and analgesic depending on dose and tested species. In this study, new phenyl and thienyl analogues with specific affinity for the phencyclidine sites in NMDA receptors, dopamine uptake blocking, or both of them were synthesized. The acute and chronic pain properties of these compounds were studied using the tail immersion and formalin tests on mice and the results were compared with control and phencyclidine groups at a dose of 10 mg/kg. The outcomes indicated that all synthesized compounds showed better activities to decrease acute thermal and chemical, but not chronic pains. Also, these effects were more significant for phenyl (group 1) compared to thiophene (group 2) analogues, which is probably due to the higher affinity of group 1 for inhibition of dopamine reuptake compared to binding to the phencyclidine sites in NMDA receptors in this family.
New morpholine analogues of phencyclidine: Chemical synthesis and pain perception in rats
Ahmadi, Abbas,Khalili, Mohsen,Hajikhani, Ramin,Naserbakht, Moslem
, p. 227 - 233 (2011)
Phencyclidine (PCP, I) and most its derivatives have demonstrated some pharmacological effects. Accordingly, in this study, the new methoxy (III) and hydroxy-methyl (IV) morpholine PCP derivatives were synthesized. The acute and chronic pain activities of these drugs (III, IV) were investigated by tail immersion and formalin tests on rats and the results were compared with those in PCP, PCM (PCP-morpholine, II), and methyl-PCM (V). Findings indicated that III (6 mg/kg, i.p.) generates more analgesic effects in tail immersion test in comparison with I and II in 20, 40, 45 and 55 min post-injection. These effects were observed in 10, 20, 40, 45 and 50 min after the application of IV (at the same dosage). This analgesic effect was markedly seen in 20, 40, 45 and 50 min after compound IVs application in comparison with the drugs (I-V). In formalin test analysis, the acute chemical pain (Phase I) could not be affected by any drugs (I-V) while chronic formalin pain would be diminished by these new synthesized drugs (III and IV), especially in late Phase II, compared to I and II at the dosage of 6 mg/kg. It is, therefore, concluded that these new synthesized PCP derivates including methoxy-PCM (III) and hydroxy-methyl-PCM (IV) could substantially and respectively diminish acute thermal and chronic chemical pains.
New amine and aromatic substituted analogues of phencyclidine: Synthesis and determination of acute and chronic pain activities
Shokrollahi, Maryam,Samadizadeh, Marjaneh,Khalili, Mohsen,Sobhanian, Seyed A.,Ahmadi, Abbas
, p. 570 - 576 (2020/01/08)
Background: Phencyclidine (PCP, I) is a synthetic drug with remarkable physiological properties. PCP and its analogues exert many pharmacological activities and interact with some neurotransmitter systems in the central nervous system like particular affinity for PCP sites in NMDA receptors or dopamine uptake blocking or even both. Aim and Objective: The following research, methyl group with electron-donating and dipole moment characters was added in different positions of phenyl ring along with the substitution of benzylamine (with many pharmacological effects) instead of piperidine ring of I to produce new compounds (II-V) of this family with more analgesic activities. Materials and Methods: Analgesic activities of these new compounds were measured by tail immersion and formalin tests for acute and chronic pains, respectively. Also, the outcomes were compared with control and PCP (10 mg/kg) groups. Results: The results indicate that compounds III, IV, and V have more acute and chronic antinociceptive effects than PCP and compound II which may be concerned with more antagonizing activities of these new painkillers for the blockage of dopamine reuptake as well as high affinity for NMDA receptors PCP binding site. Conclusion: It can be concluded that the benzylamine derivative of phencyclidine with a methyl group on the benzyl position on phenyl ring (V) is a more appropriate candidate to reduce acute and chronic (thermal and chemical) pains compared to other substituted phenyl analogs (II-IV) and PCP.
Transamination of a-amino nitriles
Popov,Mokhov,Tankabekyan
, p. 21 - 24 (2014/03/21)
α-Amino nitriles containing a primary amino group undergo transamination with aliphatic and aromatic amines under mild conditions with high yields. A probable reaction mechanism involving intermediate elimination of cyanide ion has been proposed.
Synthesis and antinociceptive behaviors of new methyl and hydroxyl derivatives of phencyclidine
Ahmadi,Kermani,Naderi,Hajikhani,Rezaee,Javadi,Niknafs
scheme or table, p. 763 - 769 (2012/06/30)
Phencyclidine (I) and its derivatives show such pharmacological behaviors as analgesic, anticonsulvant, anti-anxiety and antidepressant, while interacting with central nervous system. In this study, new methyl and hydroxyl derivatives of PCP were synthesized and their antinociceptive behaviors in animals were examined by measuring the number of writhing in a writhing test of visceral pain and the pain scores in Formalin test. Compared to control and PCP groups, findings in experimental groups indicated the new synthesized analogues (compounds II, III and V, 10 mg/kg) of PCP were able to produce more analgesic effects in formalin and writhing tests, especially for compound V. It was concluded that the new synthesized derivatives of PCP could substantially and respectively diminish acute and chronic pains.
Heterogeneously catalysed Strecker-type reactions using supported Co(ii) catalysts: Microwave vs. conventional heating
Rajabi, Fatemeh,Nourian, Saghar,Ghiassian, Sara,Balu, Alina M.,Saidi, Mohammad Reza,Serrano-Ruiz, Juan Carlos,Luque, Rafael
supporting information; experimental part, p. 3282 - 3289 (2011/12/15)
A range of α-aminonitriles could be efficiently prepared from various aldehydes/ketones and primary or secondary amines using a highly active and stable Co(ii) complex supported on different mesoporous supports at both room temperature and low temperature microwave irradiation under solventless conditions. Catalysts were also highly reusable under the investigated reaction conditions and could be reused at least 10 times without loss of catalytic activity. The Royal Society of Chemistry.
Synthesis and analgesic effects of methoxy-pyrrole derivative of phencyclidine on mice
Ahmadi, Abbas,Solati, Jalal,Hajikhani, Ramin,Pakzad, Sara
scheme or table, p. 5429 - 5432 (2012/07/27)
Phencyclidine, 1-[1-phenylcyclohexyl]piperidine (PCP, I) and its derivatives have shown considerable pharmacological effects. In this work, pyrrole derivative of phencyclidine (PCP-pyrrole, 1-[1-phenylcyclohexyl]pyrrole, II) and a new derivative (1-[1-[3- methoxyphenylcyclohexyl]pyrrole, III) and their intermediates were synthesized, then the acute and chronic pains were examined on mices at 1 mg/kg dosage using tail immersion (as a model of acute thermal pain) and formalin (as a model of acute chemical and chronic pain) tests and the results were compared with phencyclidine and control (DMSO) groups. The results indicated that III produced more analgesic effects compared to II in tail immersion test and also revealed that the newly synthesized derivative (III) significantly reduced chronic pain (especially in initial of phase II) in formalin test compared to other groups.
Discovery of a novel series of selective HCN1 blockers
McClure, Kelly J.,Maher, Michael,Wu, Nancy,Chaplan, Sandra R.,Eckert III, William A.,Lee, Dong H.,Wickenden, Alan D.,Hermann, Michelle,Allison, Brett,Hawryluk, Natalie,Breitenbucher, J. Guy,Grice, Cheryl A.
scheme or table, p. 5197 - 5201 (2011/10/02)
The discovery of a series of novel, potent, and selective blockers of the cyclic nucleotide-modulated channel HCN1 is disclosed. Here we report an SAR study around a series of selective blockers of the HCN1 channel. Utilization of a high-throughput VIPR assay led to the identification of a novel series of 2,2-disubstituted indane derivatives, which had moderate selectivity and potency at HCN1. Optimization of this hit led to the identification of the potent, 1,1-disubstituted cyclohexane HCN1 blocker, 2-ethoxy-N-((1-(4- isopropylpiperazin-1-yl)cyclohexyl)methyl)benzamide. The work leading to the discovery of this compound is described herein.
Efficient Co(ii) heterogeneously catalysed synthesis of α-aminonitriles at room temperature via Strecker-type reactions
Rajabi, Fatemeh,Ghiassian, Sara,Saidi, Mohammad Reza
supporting information; experimental part, p. 1349 - 1352 (2010/09/15)
An environmentally friendly and highly active mesoporous Co(ii) complex on mesoporous SBA-15 material could be used as an easily recoverable catalyst for the synthesis of α-aminonitriles from a wide range of aldehydes/ketones and primary or secondary amines with good to excellent conversions yields at room temperature under solventless conditions. The catalyst can be recovered by simple filtration and could be reused at least 10 times without loss of catalytic activity.
Synthesis and determination of acute and chronic pain activities of 1-[1-(3-methylphenyl)(tetralyl)]piperidine as a new derivative of phencyclidine via tail immersion and formalin tests
Ahmadi, Abbas,Khalili, Mohsen,Mihandoust, Farnaz,Barghi, Leila
scheme or table, p. 30 - 35 (2010/04/24)
Phencyclidine (1-(1-phenylcyclohexyl)piperidine, CAS 956-90-1, PCP, I) and ketamine (2-O-chlorophenyl-2-methylaminocyclohexan, CAS 1867-66-9, II) revealed some analgesic effects. Some of their derivatives have been synthesized for biological properties studies. Utilizing 1-tetralone as a starting material, 1-[1-(3-methylphenyl)(tetralyl)]piperidine, (PCP-CH3-tetralyl, III) was synthesized and its analgesic effects were studied on rats via tail immersion (as a model of acute thermal pain) and formalin (as a model of acute chemical and chronic pain) tests and compared with those of ketamine and PCP. The results indicated a marked anti-nociception 2-25 min after ketamine injection, but this analgesic effect lasted for 40 min following PCP-CH 3-tetralyl application in the tail immersion test. However, the data obtained from the formalin test showed that chronic pain could be significantly attenuated by ketamine, PCP and PCP-CH3-tetralyl. ECV·Editio Cantor Verlag, Aulendorf (Germany).
